"Osterville is home to two large boat yards, Crosby Boat Yard, builder of the original Wianno Senior, a gaff-rigged sloop once favored by President John F. Kennedy..."
...and the Crosby Catboat and Oyster Harbors Marine, both offering sales, docking and servicing of boats of all sizes.
There are two private country clubs in Osterville, the Oyster Harbors Club, located in a gated community. The Wianno Club sits on the shores of Nantucket Sound. Each club has a private 18 hole golf course, private tennis and a private beach. The Wianno Club also offers a Yacht Club with sailing for children to adults.
Points of interest:
Osterville Historical Museum
Two acres of lovely grounds with a collection of antique wooden boats, fine arts, furniture, and is a great spot for a picnic lunch.
A pleasant beach that is great for the whole family. Featuring an ocean side beach and a calmer bayside beach that's perfect for younger children, a large dock that's great for fishing and jetties to walk on.
A secluded peaceful freshwater pond with a beautiful sandy beach surrounded by a nature loving walking trails. Bonus - Only residents know about this spot.
My perfect day in Osterville, MA
Start the day at Amie's Bakery, a small town coffee shop-bakery offering homemade pastries,
wonderful sandwiches and interesting conversations.
"Walk around our special local spot, Joshua’s Pond for the peacefulness and scenery."
Lunch at Wimpy's Seafood Café, which offers award-winning chowder, great burgers, and fine seafood dishes. Stroll into Oak & Ivory, a speciality gift shop offering nautical and coastal gifts, including many handmade gifts like the popular Nantucket baskets. Walk the grounds at the Osterville Historical Museum and check out the old wooden boats. End with dinner at Five Bays Bistro, Osterville’s answer to fine dining.